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Azide⋅⋅⋅Oxygen Interaction: A Crystal Engineering Tool for Conformational Locking.

Mithun C Madhusudhanan1, Haripriya Balan1, Daniel B Werz2

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|August 16, 2021
PubMed
Summary
This summary is machine-generated.

This study reveals a consistent syn conformation between azide and oxygen groups in 36 synthesized compounds, driven by a weak, non-covalent interaction. This interaction, similar to hydrogen bonding, influences molecular structure in various chemical systems.

Keywords:
azide-oxygen interactionconformationcrystal engineeringnon-covalent interactionssupramolecular chemistry

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Crystallography

Background:

  • Azide and oxygen functionalities are common in organic molecules.
  • Understanding non-covalent interactions is crucial for predicting molecular conformation and reactivity.

Purpose of the Study:

  • To investigate the conformational preferences of molecules containing azide and oxygen groups separated by three bonds.
  • To characterize the nature and strength of the interaction between these groups.

Main Methods:

  • Synthesis and crystallization of 36 novel compounds.
  • X-ray crystallography for crystal structure determination.
  • Computational chemistry including M06-2X/6-311G(d,p) geometry optimization.
  • Quantum topological analysis (Atoms in Molecules theory).
  • Non-covalent interaction analysis (NCI-RDG plots).
  • Natural Bond Orbital (NBO) and Natural Population Analysis (NPA).
  • Molecular Electrostatic Potential (MESP) mapping.
  • Cambridge Structural Database (CSD) search.

Main Results:

  • A recurring syn conformation was observed between azide and oxygen groups in all 36 crystal structures.
  • Computational methods confirmed the syn conformation, indicating it is not solely a crystal packing artifact.
  • Analysis revealed a weak attractive interaction, characterized by bond paths and bond critical points, similar to hydrogen bonding.
  • NCI-RDG plots identified electrostatic and dispersive contributions to the interaction.
  • NBO analysis indicated minor charge-transfer contributions in some systems.
  • NPA and MESP further supported the favorable azide-oxygen interaction.
  • CSD search confirmed the frequent occurrence and conformational influence of this interaction.

Conclusions:

  • A specific azide-oxygen interaction dictates a syn conformation when these groups are separated by 2-4 bonds.
  • This interaction is a significant, albeit weak, non-covalent force influencing molecular structure.
  • The findings have implications for the design and understanding of molecules containing these functional groups.